2-(1,5-dimethyl-1H-pyrrol-2-ylmethyl)-3-oxo-1-(prop-2-ynyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid | 1022170-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,5-dimethyl-1H-pyrrol-2-ylmethyl)-3-oxo-1-(prop-2-ynyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid
• 英文别名: 2-[(1,5-Dimethylpyrrol-2-yl)methyl]-3-oxo-1-prop-2-ynylisoindole-1-carboxylic acid
• CAS: 1022170-07-5
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: YLCZYKDAGHDXHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,5-dimethyl-1H-pyrrol-2-ylmethyl)-3-oxo-1-(prop-2-ynyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid 在 silver carbonate 作用下， 以 甲苯 为溶剂， 以99%的产率得到2'-((1,5-dimethyl-1H-pyrrol-2-yl)methyl)-5-methylidene-4,5-dihydrospiro[furan-3(2H),1'-[1H]isoindole]-2,3'(2'H)-dione
  参考文献：
  名称：

  Silver-catalyzed spirolactonization: first synthesis of spiroisoindole-γ-methylene-γ-butyrolactones

  摘要：

  gamma-Acetylenic carboxylic acids are cyclized to spirolactones under mild conditions, in the presence of Ag2CO3 catalyst. The corresponding spiro-5-alkylidene-gamma-butyrolactones were isolated in high yields, and this process constitutes an easy and efficient route to analogous structures of natural products of biological interest. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.137
• 作为产物：
  描述：

  2-(1,5-dimethyl-1H-pyrrol-2-ylmethyl)-3-oxo-1-(prop-2-ynyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到2-(1,5-dimethyl-1H-pyrrol-2-ylmethyl)-3-oxo-1-(prop-2-ynyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid
  参考文献：
  名称：

  Silver-catalyzed spirolactonization: first synthesis of spiroisoindole-γ-methylene-γ-butyrolactones

  摘要：

  gamma-Acetylenic carboxylic acids are cyclized to spirolactones under mild conditions, in the presence of Ag2CO3 catalyst. The corresponding spiro-5-alkylidene-gamma-butyrolactones were isolated in high yields, and this process constitutes an easy and efficient route to analogous structures of natural products of biological interest. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.137

文献信息

• Silver-catalyzed spirolactonization: first synthesis of spiroisoindole-γ-methylene-γ-butyrolactones
  作者：Mohamed M. Rammah、Mohamed Othman、Kabula Ciamala、Carsten Strohmann、Mohamed B. Rammah

  DOI：10.1016/j.tet.2008.01.137

  日期：2008.4

  gamma-Acetylenic carboxylic acids are cyclized to spirolactones under mild conditions, in the presence of Ag2CO3 catalyst. The corresponding spiro-5-alkylidene-gamma-butyrolactones were isolated in high yields, and this process constitutes an easy and efficient route to analogous structures of natural products of biological interest. (c) 2008 Elsevier Ltd. All rights reserved.